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Isotopic labelling in the study of organic and organometallic mechanism and structure: an account
Author(s) -
LloydJones Guy C.,
Muñoz M. Paz
Publication year - 2007
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1382
Subject(s) - chemistry , palladium , cycloisomerization , reagent , salt metathesis reaction , nuclear magnetic resonance spectroscopy , enantiomer , metathesis , alkyl , allylic rearrangement , kinetic resolution , kinetic isotope effect , reaction mechanism , stereochemistry , tsuji–trost reaction , organic chemistry , catalysis , enantioselective synthesis , deuterium , polymerization , polymer , physics , quantum mechanics
An account of the use of stable isotopes ( 2 H, 13 C, 15 N, 18 O, 34 S) for the study of organic and organometallic reaction mechanism and structure, by way of kinetic determinations and modelling, NMR spectroscopy and mass spectrometry is presented. The techniques discussed include use of kinetic isotope effects, label‐facilitated nOe experiments, cross‐over experiments, stereoisotopochemical analysis, label‐facilitated NMR analysis of enantiomers using chiral‐shift reagents and NMR in chiral liquid crystal matrices. The reactions in which these tools have been applied are β‐H elimination in Pd‐σ‐alkyl complexes, the Bayliss–Hilman reaction, C–H insertion of stable carbenes, ring‐closing metathesis reactions, palladium‐catalysed hydrosilyation, palladium‐catalysed cycloisomerization, anionic thia‐Fries rearrangements, synthesis of proton sponges and their nitrogen stereodynamics, and transition metal (Pd, Mo) catalysed allylic alkylation. Copyright © 2007 John Wiley & Sons, Ltd.